Category Archives: Freelance Tips

Are You a Maker or a Seller?

Vincent van Gogh was a brilliant painter who died penniless because he wasn’t a brilliant salesman.

Sound familiar?

You’re probably no van Gogh (let’s be honest), but you do have talents.  You’re good at some things, and you may even be great at something.  But unless one of the things you’re good at is convincing other people to pay you for the work you do, it’s probable that you and Vincent do have at least one thing in common:

You’ll probably die broke, too.

Creators Are Rarely Marketers, and Vice Versa

While interviewing Matthew Ebel on the Freelance 4 Real podcast this week, I realized that those of us who are truly passionate about art and creation are often horrible at selling the very things we make.

Not only are we our own worst critics, but we’re also our own worst self-promoters, and it’s usually for the same reason: we know all the flaws in our work.

When I look at something I’ve made, I see what it could have been, and that makes it almost impossible for me to convince someone else that it’s wonderful, because — to me — it’s fallen short of what I want it to be.

Meanwhile, when someone approaches my work as a viewer, a reader, an outsider, they might love it because they have no idea what it could have been, or what I intended it to be; they can only appreciate it for what it is, or by comparing it to other things that also exist (and which have also probably been dismissed by their own creators).

So, as artists or musicians or filmmakers or other voluntary devotees of the aesthetic life, when it comes time for us to put on our business hats, we often have trouble thinking about (and pricing) our skills and services objectively.  We’re inclined to charge too little for what we do because we’re comparing our work to our own idealized version of ourselves — which is priceless — rather than pricing ourselves reasonably, or in honest comparison with our peers.

We might even feel like expecting people to pay us for our work is an affront or a burden.  (After all, we know what head cases we can really be; how can we saddle someone else with a bill for putting up with us?)

And this is why I think independent artists who have even a vague amount of self-awareness should do something radically practical:

Hire an agent.

Pay Someone Else to Pimp You

Maybe you only need one buyer or one contract to get by, or maybe you need as much work as you can handle.  Whatever the case, if you have trouble selling yourself, hire someone else to sell you instead.

An agent only makes money when you make money, which means your agent needs to find ways to sell you to the right buyer(s).  And that means your agent’s skill set is drastically different from your own.  While you might be great at creativity, problem solving and general efficiency, your agent is good at networking, pricing and sales.  S/he understands that creative types can’t see themselves for what they are, so s/he makes a business of convincing other people of how you should be seen.

And when that business model works, you both profit.

There’s a reason aspiring actors, writers and athletes rejoice the day they land an agent: it means someone with connections believes they just found an asset (AKA you) which their connections will believe is worth employing, AND it means you can now focus on your craft, rather than on convincing someone else that your craft is worth paying for.  (That’s your agent’s job now.)

But what if you’re not the kind of person who even wants long-term contracts?

What if the act of selling yourself is so unpalatable to you — even when someone else is doing it for you — that you’d almost rather revert to a 9 to 5 job than ever have to go to another pitch meeting again?

There’s a solution for you, too:

Make things that sell themselves.

Productize So You Can Prioritize

One of the dirty little secrets about freelance is that if you’re spending all your time trying to land new jobs, you’re never really focused on the work.  (When you’re part of a small agency, the same rules apply — there, your creatives are your salespeople, and they’re burning their candles at both ends.)

If chasing paychecks isn’t your idea of a fulfilling life, and if having someone else chase them for you just feels like screwing yourself with a condom on, change who you are: stop being a freelancer and start being a craftsman.

A freelancer goes where the work is.  A craftsman makes things that inspire the buyers come to him.

Sure, you still need to advertise.  And if you’re a typical self-loathing artisan (or, worse, if you’re delusional about your own talents), you may want to ask someone with a level head to do your advertising for you.

But this way you’ll be focused on making great work that people want or need, instead of needing to convince someone that you’re worth investing in over long periods of time, and then repeating that same sales cycle every time the work runs out.

As long as you keep making things that delight your audience or solve their problems, you can stay in business.  And isn’t making great work the whole reason you want to wake up in the morning?

Sometimes, freelance isn’t about convincing people you’re worth it.

Sometimes it’s about being worth it, and then handing out maps so people can find you.

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7 Business Tips I Learned by Interviewing 7 Freelancers

You probably know I’m a freelancer.  You may also know that Mike Sorg and I co-host a weekly podcast called Freelance4Real, where we interview our fellow freelancers (and each other) about the ups and downs of the freelance working world.  Our shows cover everything from programming to photography, travel to taxes and motivation to marriage, all under the umbrella of freelance success.

But if you’ve never heard the show, you probably don’t know what we know, which is a lot more than we did when we started.  To wit, here are some business tips we’ve learned from our first few guests.

1. Sometimes you need a buffer between you and your clients.

Web designer John Carman of Avenue Design Studios learned a valuable lesson early in his freelance career: sometimes not being the point of contact for a client can make a job easier.  In this episode of the show, he suggests employing a project manager to oversee communications, blunt the review criticisms and keep all parties happy and moving forward, as well as offering some tips on generating client referrals.

2. There’s always enough time; you just have to find it.

“I’d love, to do more, but…” is one of the biggest hurdles most people encounter on their quest to start (or succeed) as a freelancer.  So take it from social marketing manager Molly White, who’s a full-time entrepreneur and a full-time mom: it can be done.  In this episode, Molly — whose specialty is helping small businesses figure out Facebook — shares her tips on how to pitch good ideas to skeptical clients, and how to succeed as a freelancer without forsaking your family.

3. Incorporating might be the smartest choice for your business (and your marriage).

Josh and Rachel Sager each have full-time jobs and freelance clients, and since their individual skill sets complement each other — he’s a programmer and web designer, she’s a graphic designer — they decided to launch their own LLC, Second Block Studio, to work on projects together.  But before they did, they consulted with a lawyer who helped them find the best way to protect their business and their sanity.  In this episode, they shared tips for finding a good lawyer, filing the right papers, separating work time from playtime and how to stay sane while working together.

4. Know your rights — including the ones you wrote into your own contract.

Don Orkoskey of WDO Photography told us he escaped into freelance because his day job felt like prison.  Now he makes a living as a photographer, and the co-founder of animation venture The Schmutz CompanyIn this episode, Don shares tips on everything from getting started as a freelance photographer to the importance of client contracts — and what to do if a client violates yours.

5. Your pay rate is allowed to scale, but that’s your choice, not your client’s.

Programmer Scott Connelly became a freelancer when he was downsized from his day job.  Making that change meant he had to earn as much income from a variety of new clients as he once did from a full-time paycheck.  In this episode, Scott talks about how to hit the ground running if the same thing happens to you, and how to build conditions into your contracts that allow you to still profit from jobs that may not meet your normal rates.

6. Your cost of living determines your freelance future.

Steve Klabnik dropped out of college to help found a startup and then transitioned to freelance programming.  Today, he travels the country to speak at coding conferences, where he generates leads and then vets potential new ventures online using the lean startup method.  In this episode, Steve explains how keeping his overhead amazingly low has granted him the ultimate freedom in his career, and why going to school may be a horrible idea.

7. Know when to say “no” to an opportunity.

Actress Robyne Parrish makes a living on stage, TV, film, web and in print.  She also founded the Sonnet Repertory Theatre company in New York City, teaches theatre in Pittsburgh and North Carolina, and directs plays across the eastern US.  In this episode, she offers great advice for aspiring actors and actresses on everything from finding (and firing) an agent to figuring out which jobs are worth traveling for and how to balance the work you want to do with the work you need to do — lessons that actually apply to freelancers from all fields.

You can listen to any episode of Freelance4Real at your leisure, or subscribe on iTunes.

And if you’re online on Tuesdays at 4 PM EST, you can listen to the show live at  (NOTE: That’s the link Sorg uses to stream all his shows while he records them, so if you click that link at any time other than Tuesdays at 4 PM EST, you never know what you’ll get.  It could be Awesomecast, it could be the Wrestling Mayhem Show, it could be nothing at all.  Sorg is a man of many interests, and occasional sleep.)

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11 Reasons You Always Procrastinate (and How to Stop)

As I mentioned recently, I talk a lot about procrastination and distraction because that’s currently my big stumbling block.  Judging by the comments on those posts, I’m not alone.

But why are we such chronic procrastinators?

Lately, I’ve been trying to identify why I feel the urge to click away from what I should be doing and go do something — anything — else.  And I think I can identify a few clear patterns.

Does any of this sound familiar?

1. Facebook and Twitter are fun.  Damn them, social media channels are a far more enjoyable way to fritter away my day than any actual work could possibly be.  And when you work in social media (like I do), you’re doubly screwed by this fact.

2. My tabs are open.  If I keep seeing that new (1) in my Gmail, Twitter or Facebook tab, I’m going to click over and see what’s new.  Because I like new, and I like validation.  And that (1) could be anything.  I’ve said before that I loved college because I knew anything could happen there, on any day, which made every day an adventure.  Sadly, the (1) is as close as I get to that feeling today.  It’s a tantalizing future in parentheses, dozens of times a day.  How can I not click?

3. Page loads kill my day.  You’d be surprised how often I click out to Twitter, Facebook or email instead of waiting for something as simple as a blog preview or a video render — which might take as little as 5 seconds — to load.  Because those are 5 seconds I could use to catch up on a Twitter conversation I’ve been half-having… except that 5 seconds turns into 20 minutes, and then it’s time for lunch, and then a nap, and then…

4. I feel obliged to be entertaining.  I have nearly 6000 Twitter followers, and I like to imagine they’re hanging on my every word, rejoicing when I share something amusing or meaningful that brightens their otherwise mundane days.  (I wish I could say I get the same value from them, but in fact, I rarely check my timeline because I’m too busy trying to find things to share with them. If I read more tweets, I’d never accomplish anything.)

5. Actual work requires more mental capital than distractions do.  Accomplishing something meaningful in my day will likely require effort, dedication and tunnel vision.  But racking up a bunch of “quick touch points” in social media seems like I accomplished something, doesn’t it?  It’s easier to get that 10% dopamine rush repeatedly throughout the day than it is to bear down and work my way to 100% through “actual” work.

6. The endless loop.  Check my multiple accounts on Gmail, Twitter, Facebook, YouTube, Favstar, blogs, etc.  Leave comments, answer questions, ask a few.  Find something to share.  See who else shared it.  Answer an email.  Refresh.  Repeat.  (All day.)

7. No consequences.  Really, if I did want to just watch YouTube videos all day, I could.  I’m self-employed.  If I want to screw myself and scramble to pay next month’s rent, I can.  It’s my choice.  Social media is freedom, and I naturally feel obligated to milk it for all it’s worth.  If I had an employer who was holding me accountable for my workday, I’d be using social media as a reward or an escape between deadlines, rather than elevating it to its current status as a time-sucking lifestyle.  But, as my own boss, I have a patriotic right to watch one more YouTube video.  That’s why we fight the wars, isn’t it?

8. Too many stepping stones, not enough Lambada. Let’s say I have a goal, and reaching it requires me to accomplish 5 small tasks, in a specific order.  If I won’t feel the rush of a payoff until I do all 5, I’m less likely to start on 1 than I am to spend the next hour dicking around on Facebook, because not enjoying those first 4 steps will feel the same whether I start them now or later.

9. If I don’t have a plan that’s guaranteed to succeed, I have less reason to follow it.  If those 5 steps lead to me getting paid, then I’m going to follow them (eventually).  But if, as a freelancer, those 5 steps might lead to me getting paid or they might not, then following them is a crapshoot.  I might as well just browse Chainsawsuit for ten minutes instead...

10. I don’t even know what the next step is.  I may have a mile-long to do list, but if step 1 for each of those tasks isn’t clearly spelled out, I have no clear understanding of what I should be doing next.  And taking the time to figure out that whole process is a process, and that takes time.  But liking my friend’s adorable puppy photo on Facebook?  I understand the ROI on that

11. Writing about distraction is a distraction.  When I blog about distraction, I get a huge traffic spike.  Tell me that’s not a fucked up Pavlovian habit to get hooked on.

So, what do I — and we — do?

We kill it.

All of it.

Three Ways to Blow It All Up and Feel Like an Action Hero

[NOTE: I feel compelled to point out that, as I typed the above sentence, I felt the urge to click away and cycle through my social media tabs.  Seriously.  While writing a post about distraction, I had to fight the urge to check in on Facebook to see if I was missing out on something more important.  I swear, this social media mindset is insidious...]

Yes, Virginia, there is a Santa Claus.  And he gets shit done.

Here’s how.

A) Grab the Nearest Problem and Solve It.

My girlfriend and I work notoriously poorly together, because I’m a process-based person and she’s a “do what’s closest at hand” kind of person.  I can be concocting a strategy for accomplishing a massive project and she’ll derail me by asking me to clean the bathroom because we have guests coming in five days.  My mind is boggled by her inability to focus on the long view, and she’s irritated by my reliance on lists and processes (which I spend more time rewriting than carrying out).

Funny enough, some philosophies indicate she may be right.

Remember how I said I’m less likely to start step 1 of a project if the process (or payoff) isn’t clear?  If I were really smart, I’d just dive in and get started anyway, because by doing so, I’d be one step closer to success or failure, rather than sitting here staring at it.  And by that rationale I can fail 4 times and succeed once in the time it would take me to write another, “better” to-do list.

B) Work without the Internet.

It’s no secret that I get more done when I’m not online.  I also think more clearly when I’m not plugged in.  I actually used to enjoy editing video at Starbucks in the days before free wi-fi because I knew I could sit there for a few hours and not be able to check my email.

If you’re as socially-addicted as I am, nuke it.  Work without it.  Go someplace where there’s no web connection.  Leave your smartphone at home.  Block your most-visited websites.  Yes, it’s extreme, but if your problem is as extreme as it increasingly seems like ours is, you’re not going to put that fire out with a flyswatter.

3) Cut All Your Losses Except One.

One of the reasons I’m so distracted is because I’m overwhelmed.  I’m juggling half a dozen separate ventures right now, all of which are competing for my time, attention, energy, expertise and resources.  Some of them pay, some of them could, and any of them could be something I could do full time… but none of them are.  Yet.

And so I do all of them half-assedly.

Really, I should kill one.  Or all of them but one.

If I did that, I’d reduce my to-do list exponentially.  I’d only be responsible for one route to success, which I could commit to fully, rather than hedging my bets and basing my expectations on what I can do with 20% of my time, rather than 100% of my time.

Paradoxically, the more I have to do, the more I embrace distractions because I start to feel like those distractions are “my choice,” rather than what they really are, which is “the wall I’m building between myself and success.”  If I won at one of the ventures I’m fueling, I wouldn’t need distractions to create cheap thrills; I’d have the real thing.

And who knows what that could lead to?

So, if you want to do more, start doing less.  But do all of it.

The Fourth Option

Also, I have identified a fourth solution which I haven’t mentioned yet, because I’m a few weeks away from being able to discuss it clearly.  I have too many variables in play right now to make a proclamation just yet, but I strongly suspect this approach will work for me, and maybe for you, too.  So stay tuned…

… but not too closely.  You have work to do.

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Why I’m Ruthlessly Downsizing My Life

I’m a process-based person.  I love lists.  I also love a good curriculum, because I thrive on following directions (or improvising my way past them) and on meeting or exceeding other people’s expectations.

So, last night, I did something shocking — to me, anyway.

I removed Sports Illustrated from my bookmarks toolbar.

For Want of a Bookmark, the Battle Was Lost…

If you’re not me, this doesn’t seem shocking.  But if you are me, and you’ve had Sports Illustrated bookmarked on every browser you’ve used since 2000, this is quasi-apocalyptic.

Why the change?

Because I’m sick of not succeeding.

See, I’ve been observing myself a lot lately, and I’ve noticed something odd about my work habits:

I don’t have any.

Instead, what I have are habits for avoiding work.

For example, I have a toolbar filled with bookmarks that are supposed to save me time, but they really just make my daily distractions more attractive.  “Of course I have time to read an article on Grantland,” I’ll say.  But I don’t.  Not really.  Not if I actually want to get everything on my to-do list — or even a handful of those items — done.

(Which is why I just removed Grantland from my toolbar too.)

Great, So I’m Becoming a Luddite. Why Bother?

Because I’ve noticed something really disturbing about myself: I’ve trained myself to expect pleasure from distractions.

I’m pretty sure you do this too.  Instead of buckling down and getting something done and then rewarding yourself with a break, you take the break first.  You procrastinate, because you’ve convinced yourself that there’s always more time.

But there’s not.

I have some things on my to-do list that have been written there since I lived in Pittsburgh, and yet I moved to Baltimore in 2009.  That means those to-dos are ancient.  And, sadly, they haven’t even become irrelevant in the ensuing two years.  They’re still totally valid.  I could accomplish them tomorrow and tangibly improve my quality of life.

Or, I could refresh Facebook and see if anyone liked something I shared.

Same thing, right?

Pavlov’s Dog Would Have LOVED Twitter

The tiny burst of dopamine I get from interactions on social platforms carries a disproportionate weight in my mind, because…

  • I work in social media, so it’s nice to know I’m doing it right.
  • I freelance, so most of my socializing occurs online.
  • I enjoy having my thoughts, ideas and punchlines validated by others.

And since the business of social media and the personal side of social media are so often indistinguishable, I can tweet for an hour and reasonably convince myself that I just simultaneously did work and took a break… but I won’t feel fulfilled by either measure, so I’ll just do it again.

… and again.

Every Time You Tweet, You Change the World

Or you could.

Because you never know how something you said, made or shared across one of your social channels will be received.

Will this be the time I become wildly popular, or connect with someone who has real cultural cachet, or accidentally stumble headfirst into a job opportunity or social clubhouse that no one else knows about, all because of something witty or relevant that I mentioned on CoTweet?

It could be.


It’s not?

Well, I’ll just try again…

Change Your Stars One Point at a Time

Ultimately, a process is only as useful to a person as her habits will allow it to be, so the quality of our habits is in many ways a more important compass for our success than the quality of our process itself.

Now, let’s be clear: I’m not crazy enough to believe that removing a few bookmarks will in any way keep me from distracting myself from my actual goals.  Thanks to the magic of Firefox, I really just need to type “si” into my browser’s address field and it’ll pull up all the Sports Illustrated pages I could ever never want.  Those bookmarks were, in many ways, redundant.

But their absence is intended to change my behavior.

Because now, instead of clicking one button and being whisked away to Never Never Getting Any Work Done Land, I actually have to type letters into my browser.  And I’m betting the act of consciously typing even one letter will ring whichever time management alarm in the back of my brain that gets so conveniently short-circuited whenever I click on those bookmark buttons.

This is just one of several ways I’m streamlining my life and establishing new processes to refocus myself on the things my younger self thought I would have accomplished by now.  I’ll revisit this topic again soon, once I have enough experience to know if my new habits and processes are working (for me) well enough to be worth sharing.

In the end, while I’m really sick of not succeeding, I’m even sicker of not failing.

I mean, if I were succeeding? Great!  And, if I were failing, at least I’d know I was doing something wrong, and then I’d have an opportunity to change courses or improve.

But neither succeeding nor failing means I’m just treading water.  And since that’s not a particularly enthralling way to spend my life, I’m going to change my habits in order to change my direction.

After all, it takes just as much energy to run in place as it does to run forward.

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Accidental Business Advice from Spider-Man Creator Stan Lee

How many of your ideas have been overnight successes?


Sorry to hear that.

But hey, don’t give up.

You might just be on a lifetime odyssey toward incredible success.  And you could do worse than to remember a word of advice from a guy whose creations were once unceremoniously destroyed by mothers around the country, only to wind up seeing his work become a cultural touchstone around the world and the fuel for some of the highest-grossing films of all time.

Face Front, True Believers…

My friend Dawn went to the Baltimore Comic Convention this weekend and was in the audience for Stan Lee’s “panel,” which was actually just Stan Lee answering questions from people.  While she was there, she shared a few of his more quotable comments via Facebook, like…

“People 30 years ago thought comic books were for illiterate adults and children. Today, comic writers and artists win top awards and honors. [Comics] weren’t meant for kids then and they aren’t now. I did everything I could to make sure of that.” – Stan Lee

If you don’t know who Stan Lee is, he’s the godfather of modern comic books.  As the co-creator of Spider-Man, The X-Men, The Fantastic Four and pretty much every other major (and minor) Marvel Comics character invented in the 1960s, he dragged the concept of “invulnerable” heroes like DC’s Superman, Batman and Wonder Woman into the “real” world, saddled them with real-life problems, and gave birth to the modern superhero.

For that, his work was considered a cultural distraction at best and a perversion at worst, and kids’ comic book collections from the ’60s rarely survived the decade — which is one of the reasons those issues that weren’t thrown away by fastidious moms and oblivious teens are now worth millions of dollars.

Now, almost fifty years later, Marvel (and, to a lesser extent, DC) are finally seeing their flagship characters turned into box office-smashing, record-setting, franchise-launching, globally dominant films.

But it didn’t happen overnight.

It happened because generations of fans wanted it to happen, and because the enthusiasm for these characters has been transferred from the children of the ’60s to their own kids and grandkids, who now have the buying power and the technological wizardry at their fingertips to being these stories to life in a manner that deserves global attention.

This wasn’t always the case.  Comic book fans (and creators) have suffered insults and social marginalization for decades, and the sudden acceptance of their lifelong passions at the box office doesn’t exactly make up for things like this.  But it does verify what they’ve known all along: that what they loved is worth loving, and will continue to be worth loving even after it falls out of pop culture favor, which it surely will.

Can you say the same thing for your brand / business / products / passion?

Are you willing to go the distance to see your vision succeed?

Instant Karma Is Probably Not Going to Get You

Our current digital age may give you the impression that success is either instantaneous or impossible, and that there is no in-between.


In fact, most of your ideas will fail.

Success is difficult, and the combination of skill, determination, industriousness and sheer luck that’s required for most ideas to break even is astounding.  (And if you want to be profitable, it’s even harder.)

Granted, it can be done.  But it rarely happens overnight.  (Not that I’d mind if Hollywood suddenly tried to buy The Baristas from me.  But really, we’re just getting warmed up…)

Unfortunately, most people see a lack of immediate viral success as proof that an idea, product or business model “doesn’t work,” when all it really means is that it hasn’t worked yet.  Figuring out why that is, and what might need to change, is what separates the successes from the could-have-beens.

So, why might your idea not be catching fire just yet?  Maybe you’re…

  • underfunded?
  • badly organized?
  • ahead of your time?
  • fighting an uphill battle?
  • spreading yourself too thin?
  • profiting at too small a margin?
  • battling negative public perception?

… and so on.

There’s no shortage of reasons why your ideas may not be working, which is why it’s actually a rarity when they do work.

One way to make sure you’re on the right track?

Study the competition.

Why Captain America Needs Superman (and Vice Versa)

“The last Batman was a GREAT movie. A GREAT movie. You always have to know what the competition is doing. Just wait until you see the Avengers!” — Stan Lee

In the 1960s, Stan Lee brought a fresh perspective to a super hero genre that had been rendered toothless by federal investigations and voluntary self-censorship.  Lee’s innovation was to give comic book fans something they didn’t even know was possible: characters they could relate to, rather than idolize.

The resulting boom in interest among comic fans in the ’60s led to a resurgence in super-hero cartoons, toys and TV series, but Marvel’s legitimacy at the box office was harder to come by.  Despite the relative success of the film adaptations of DC’s Superman and Batman in the ’70s and ’80s, it took Marvel another 20 years to get Spider-Man right — and when they did, they completely obliterated what audiences could reasonably expect from a comic book movie.

And then they blew itRepeatedly.

And yet, if Marvel had given up when things looked darkest, we might never have had Iron Man, which reminded the world that comic book adaptations didn’t have to suck.  And with Iron Man justifying the genre’s existence, audiences were willing to take DC’s Dark Knight seriously.  (Very seriously.)

Thus, a lesson: even when you’re winning, you’ll still find stumbling blocks.  Fight through them.  They’re called “stumbling blocks,” not “career-enders.”

Of course, it helps if you can keep your eye on the prize…

Know What Success Looks Like, So You Can Aim Properly

Q: “If you could be sucked in to one comic book world, which would it be?”

A: “Archie comics. Then I could be with Betty AND Veronica! And no super villians trying to kill me. Perfect!” – Stan Lee

Maybe your idea of success is breaking even.  Maybe it’s profitability.  Maybe it’s selling your idea or company for millions of dollars.  Maybe it’s just getting your foot in the door.

Whatever success looks like for you, that’s the benchmark against which you should be judging yourself and your work.  Not how well the competition is doing (although they do give you an idea of what’s possible).  Not arbitrary metrics that don’t satisfy your stated goals.  And not just money, because if you wanted to be filthy rich, there are plenty of ways to do it without embarking on a career-long roller coaster ride of self-doubt.

You’re doing what you do because you love to do it.  (Right?)

And that means your idea of success will be different from mine, or from anyone else’s.

The thrill is in getting there — no matter how long it takes.


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